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| 2/5/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 4th | - | 1st | 27th (DNF) |
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| 2/6/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 1st | - | - | 4th |
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| 2/7/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 3rd | - | - | 17th |
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| 2/8/2019 | Volusia Speedway Park - De Leon Springs, FL DirtCar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 2/11/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | - | 11th |
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| 4/12/2019 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 3rd | - | - | 11th |
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| 5/10/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Will Krup (A Modifieds) | 3rd | - | - | 6th |
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| 5/27/2019 | Macon Speedway - Macon, IL Mueller Dist. Miller Lite Twin 50s (Super Late Models and Pro Mods) & City of Macon Night DIRTcar Late Models, DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | - | 14th (DNF) |
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| 6/13/2019 | Kankakee County Speedway - Kankakee, IL DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models | Results | | Will Krup (DIRTcar UMP Modifieds) | 3rd | - | - | 2nd |
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| 6/18/2019 | Jacksonville Speedway - Jacksonville, IL DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models | Results | | Will Krup (DIRTcar UMP Modifieds) | 5th | - | 1st | 9th |
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| 6/20/2019 | Spoon River Speedway - Canton, IL DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models | Results | | Will Krup (DIRTcar UMP Modifieds) | 3rd | - | - | 4th |
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| 6/22/2019 | Fairbury Speedway - Fairbury, IL UMP Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models, DIRTcar Sportsmans | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | - | 7th |
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| 6/25/2019 | Tri City Speedway - Granite City, IL "Summer Nationals" MAKEUP from 6/21st UMP LM $7,500/UMP Summit Mods $1000/B-Mods $1000 DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models, B Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 1st | - | - | 5th |
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| 6/26/2019 | Peoria Speedway - Peoria, IL Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models, B Modifieds, Hornets | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | - | 5th |
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| 6/28/2019 | Terre Haute Action Track - Terre Haute, IN World Of Outlaw LM vs. Summer National LM Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Will Krup (DIRTcar UMP Modifieds) | 1st | - | - | 2nd |
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| 7/5/2019 | Merritt Speedway - Merritt, MI Fan Appreciation Night DIRTcar Late Models, DIRTcar UMP Modifieds, Factory Stocks, Stock Cars, Sportsmans, B Modifieds, Lightning Sprints, Generic 1, Mini Wedge | Results | | Will Krup (DIRTcar UMP Modifieds) | - | - | - | 2nd |
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| 7/11/2019 | Tri City Speedway - Granite City, IL "Hoker Trucking Best in the Business 50" Lucas Oil Late Models $12000/UMP vs AMS Modifieds $2000 Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 3rd | - | - | 8th |
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| 7/12/2019 | Tri City Speedway - Granite City, IL "NAPA Know How 50" Lucas Oil Late Models $12,000/UMP Crate LM $1,000/UMP vs AMS Modifieds $2000 Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar Late Models, DIRTcar UMP Modifieds, Pro Late Model | Results | | Will Krup (DIRTcar UMP Modifieds) | 3rd | - | - | 4th |
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| 7/13/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO Federated Weekly Racing Series DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Sport Compact, B Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | - | 2nd |
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| 7/25/2019 | Lincoln Speedway - Lincoln, IL UMP Summernationals & Graue Chevrolet Showdown Part 2 DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models, B Modifieds, Street Stocks | Results | | Will Krup (DIRTcar UMP Modifieds) | - | - | - | 20th (DNF) |
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| 7/26/2019 | Fairbury Speedway - Fairbury, IL WORLD OF OUTLAWS PDC SHOWDOWN Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Late Models | Results | | Will Krup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 7/27/2019 | Fairbury Speedway - Fairbury, IL 30TH ANNUAL WoO PRAIRIE DIRT CLASSIC Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Late Models | Results | | Will Krup (DIRTcar UMP Modifieds) | - | - | - | 5th |
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| 8/3/2019 | Portsmouth Raceway Park - Portsmouth, OH Lemley Motorsports presents Mod Squad Spectacular DIRTcar UMP Modifieds, Dirt Late Models, Economy Late Models, Limited Sport Mod | Results | | Will Krup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 8/10/2019 | Merritt Speedway - Merritt, MI American Ethanol Modified Tour DIRTcar Late Models, DIRTcar UMP Modifieds, Factory Stocks, Stock Cars, Sportsmans, Lightning Sprints, Generic 1, Mini Wedge | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | - | 2nd |
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| 8/16/2019 | Paragon Speedway - Paragon, IN MSCS Sprints, Paragon Sprints, Modifeds, & Hornets DIRTcar UMP Modifieds, 410 Sprints - Non-Winged, Hornets | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | - | 1st |
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| 9/7/2019 | Lincoln Park Speedway - Putnamville, IN Gary Ricketts Memorial - Buckeye Bob 33 Lap Modified Feature DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | - | 2nd |
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| 9/26/2019 | Tri City Speedway - Granite City, IL Summit Mod Mania Night #1- UMP Modifieds $3,000/UMP Late Models $3,000 DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 3rd | - | 2nd | 18th |
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| 9/27/2019 | Tri City Speedway - Granite City, IL Summit Mod Mania Night #2 - (AMS Modifieds Championship) vs UMP Mods $5,000/UMP Late Models $3,000 DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 2nd | - | 2nd | 5th |
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| 9/28/2019 | Tri City Speedway - Granite City, IL Summit Mod Mania Night #3 - UMP Modifieds $5,000/UMP Late Models $5,000 DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | 3rd | - | 3rd | 20th |
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| 10/4/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO DIRTcar Fall Nationals DIRTcar UMP Modifieds, Factory Stocks, B Modifieds, Pro Late Model | Results | | Will Krup (DIRTcar UMP Modifieds) | 7th | - | 6th | 6th |
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| 10/5/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO DIRTcar Fall Nationals DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, B Modifieds | Results | | Will Krup (DIRTcar UMP Modifieds) | - | - | - | 1st |
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| 12/19/2019 | The Dome at America's Center - St. Louis, MO 4th annual Arizona Sport Shirts Gateway Dirt Nationals presented by O’Reilly Auto Parts Midgets, Dirt Super Late Models, A Modifieds | Results | | Will Krup (A Modifieds) | 6th | - | 1st | 18th (DNF) |
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| 12/21/2019 | The Dome at America's Center - St. Louis, MO 4th annual Arizona Sport Shirts Gateway Dirt Nationals presented by O’Reilly Auto Parts Midgets, Dirt Super Late Models, A Modifieds | Results | | Will Krup (A Modifieds) | - | - | DNS | - |
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